Cover of Hollywood Nights: An Escort's Diary

Hollywood Nights: An Escort's Diary

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okays! hear me out! let’s do a book where i’m a male escort for hollywood male actors (whether they’re openly gay, in the closet, or straight). they pay me, and i’m there to give them a good time (and since im a bottom, everyone in this story will be a top). so, i was thinking each chapter will be different actors hehe!

Chapter 3: Stephen Amell

The scent of the hotel was a universe away from Alan’s penthouse—less citrus and sex, more polished marble and sterile money. Kenny rode the private elevator up, the silence a physical pressure in his ears. He’d showered twice since that morning, but a phantom ache remained, a deeper imprint than any bruise. The half-million sat in his account like a live wire. He smoothed his shirt, a simple black linen, and felt the chameleon’s skin settle over him, flexible and cool.

The door to the Wilshire suite was ajar.

He pushed it open into a wall of heat. The air was thick, deliberately stuffy, heavy with the damp-earth scent of extinguished candles and human sweat. The vast living area was dim, lit only by the last fiery embers of a sunset bleeding out over the Hollywood Hills.

A figure stood at the window, silhouetted against the dying light.

Stephen Amell turned. He was, as the synopsis had said, half-naked. A white towel was knotted low on his hips. His torso, a detailed canvas of ink and hard-earned muscle, glistened with a fine sheen of perspiration. He held a remote, pointed at a sleek unit on the wall. With a final click, a faint mechanical whir died. The room’s ambient hum ceased completely, leaving a ringing, intimate silence.

“Kenny. Right on time.” Stephen’s voice was warmer than expected, less studied than Alan’s growl. He tossed the remote onto a plush sofa. “I turned off the AC. I like the heat. Makes everything feel… more real.”

“It’s your world,” Kenny said, his smile easy, professional. He let his eyes appreciate the view—both the man and the cityscape behind him. “It’s certainly memorable.”

Stephen ran a hand through his damp hair, a gesture that seemed genuinely nervous. “Can I get you a drink? They stocked the bar with this Japanese whiskey that’s smoother than anything.”

“I’m good, thanks.”

“Right. Okay.” Stephen exhaled, a short, sharp burst of air. “Let me… show you around. Not that there’s much to see.” He gestured, leading Kenny past the grand piano, the unused bar, towards the bedroom doorway. The tour was perfunctory, an excuse to move. Kenny followed, noting the tightness in Stephen’s shoulders, the way his eyes kept flicking to a small leather case on the dresser inside the bedroom.

The bedroom was an opulent cave. Silk sheets, the color of charcoal, were turned down. More candles, unlit. The air here was even closer, smelling of starch and anticipation.

Stephen stopped in the center of the room, his back to Kenny. The muscles in his back flexed as he braced himself. “So. The thing is.” He turned around. The charming, affable mask had slipped, revealing something raw and uncertain beneath. “I have a… a specific thing. A kink, I guess you’d call it.”

Kenny leaned against the doorframe, giving him space. “Tell me.”

“I’m always in charge,” Stephen said, the words coming out in a rush. “On set, with the PR people, with the fucking trainers and dieticians. Everything is a negotiation, a performance. I’m the one who has to be… solid.” He looked directly at Kenny, his eyes clear and painfully earnest. “I don’t want to be in charge tonight. I don’t want to have to think.”

He walked to the dresser, picked up the leather case. He opened it. Inside, nestled in black velvet, were a pair of wide, padded cuffs and a simple black blindfold.

“I want to give it up,” Stephen said, his voice dropping to a near-whisper. “All of it. I want you to take it. I brought these. I’ve never… I mean, I’ve thought about it. A lot. But never actually…” He trailed off, holding the case like an offering.

Kenny pushed off the doorframe. The professional part of him catalogued the request: a power exchange, relatively simple, a common fantasy for men of his stature. The other part of him, the part still vibrating from Alan’s claiming, felt a strange twist. From being pinned to a wall to being handed the reins in a stifling hotel room. He approached Stephen slowly, taking the case from his hands. He let his fingers brush Stephen’s.

“You want to surrender,” Kenny said, not a question.

“Yes.” The relief in Stephen’s voice was palpable.

“Then we surrender.” Kenny set the case down. He reached up, his movements deliberate, and placed his hands on Stephen’s heated shoulders. He could feel the slight tremble beneath the skin. “The cuffs are for you. The blindfold is for you. This,” he said, his voice lowering, shedding its pleasant warmth for something more direct, “is for you. But I’ll be holding the ends. Understand?”

Stephen swallowed, a sharp click in the quiet. “Yes.”

“Good. Lie down. On your back.”

Kenny watched as Stephen obeyed, moving to the bed with a athlete’s grace even now. He lay back against the dark silk, his chest rising and falling a little too fast. Kenny picked up the cuffs. He sat on the edge of the bed, the mattress dipping under his weight. He took Stephen’s right wrist, fastened the padded leather around it securely, not tight enough to hurt, but with a definitive, final click. He repeated the process with the left, then tethered both cuffs to the sturdy posts of the headboard with the attached straps. Stephen’s arms were stretched slightly, his powerful frame rendered open, vulnerable.

Lastly, the blindfold. Kenny leaned over him, blocking the faint light. He saw Stephen’s eyes, wide and trusting, fixed on him. He settled the soft black cloth over them, tying it snugly at the back of his head. The world was taken from him.

Stephen’s breathing hitched. “It’s dark.”

“It’s supposed to be,” Kenny said, his voice close to Stephen’s ear. “Now you feel. Just feel.”

He started with his hands, tracing the lines of Stephen’s tattoos without seeing them, following the topography of muscle and bone. He mapped the ridges of his abdomen, the curve of his pectorals, the sensitive dip of his collarbones. Stephen flinched at the first touch, then melted into it, a low groan escaping his lips as Kenny’s thumbs circled his nipples, pinching them to stiff peaks.

“You have no idea what it’s like,” Stephen mumbled, his head turning blindly on the pillow. “To just… receive.”

“Don’t talk,” Kenny instructed softly. “Just feel the heat. Feel my hands.”

He stood, shedding his own clothes, letting them pool on the floor. The contrast was acute: him, slim and in control; Stephen, the bound, glistening monument.

Kenny climbed onto the bed, kneeling beside him. He lowered his head, his lips a whisper from Stephen’s skin. He didn’t touch yet. He let Stephen feel the ghost of his breath, the heat of his nearness in the already sweltering room. Stephen’s stomach clenched in anticipation.

“Okay,” Kenny murmured, more to himself than to the bound man. Then he kissed him.

It was not a claiming like Alan’s. It was an exploration. His mouth was soft, questioning, moving over Stephen’s with a languid patience. Stephen responded hungrily, arching up into it, but Kenny controlled the depth, the pace, pulling back just as Stephen sought more. He trailed his lips away from Stephen’s mouth, down the strong line of his jaw, to the pulse hammering at the side of his neck.

There, he licked. A slow, wet stripe from collarbone to ear. Stephen gasped. His hips bucked off the bed, a helpless jerk.

“Sensitive here,” Kenny observed, his voice a low hum against Stephen’s skin. He did it again, then sealed his mouth over the spot, sucking gently. Stephen cried out, the sound echoing in the soundproofed room. His cock, already stiff and leaking onto his towel-wrapped stomach, twitched visibly.

Kenny moved lower. He mapped the expanse of Stephen’s chest with his tongue, tracing the outlines of muscles and ink. He circled one nipple, then the other, breathing hotly over the tight nub before finally taking it into his mouth. He suckled, lightly at first, then with more pressure, grazing it with his teeth.

“Fuck! Jesus,” Stephen choked out, his back bowing. “Right there. Oh god, right there.”

Kenny lingered. He devoted what felt like decades to Stephen’s nipples, switching between them, lavishing them with attention until they were swollen, ruby-red peaks. Stephen’s pleas became a constant, ragged soundtrack. Every flick of Kenny’s tongue, every gentle bite, sent shocks straight to his straining cock.

Kenny’s hand finally strayed downward. He unwrapped the towel, tossing it aside. Stephen’s cock sprang free, thick and flushed, veins standing in clear relief. Kenny wrapped his fingers around the base, his grip firm. He didn’t stroke. He just held.

“Please,” Stephen begged, his voice shattered. “Please, Kenny. Touch me.”

“I am touching you,” Kenny said, giving a barely-there squeeze. He began to move his hand then, a torturously slow up-and-down glide, his palm damp with the pre-come beading at the tip. He set a rhythm that was pure agony—just enough friction to stoke the fire, never enough to quench it. He’d bring Stephen right to the cliff’s edge, his balls tightening, his breath seizing, then stop completely, letting his hand go still while he returned his mouth to a nipple.

An hour dissolved in this liquid state of torment. Stephen’s body was sheened in a new layer of sweat, his muscles quivering with sustained tension. He babbled, promises and curses tumbling together. “I’ll do anything, just let me come. I need it. I’m gonna die. Please, fuck, please, I’m so close.”

“You’re not close until I say you are,” Kenny would reply calmly, before taking him back to that frantic edge with a few expert strokes.

Kenny finally moved, positioning himself between Stephen’s spread legs. He reached for the lube on the nightstand, the sound of the cap snapping open obscenely loud. He prepared himself quickly, his own need a secondary thread in the tapestry of Stephen’s desperation. He notched the head of Stephen’s cock against his entrance, and without ceremony, sank down onto him in one slow, inexorable slide.

Stephen screamed. It was a raw, shattered sound of total overwhelmed sensation. Kenny took him to the hilt, seated fully, letting them both adjust to the blistering tightness. Then he began to move.

He rode him with a mesmerizing, rolling rhythm. Up, almost letting him slip out. Down, swallowing him whole. He used his hands to explore the landscape he’d memorized—skating over the damp, hard abs, cupping the heavy pectorals, pinching the over-sensitized nipples until Stephen sobbed.

“You feel fucking incredible,” Stephen groaned, his head thrashing side to side on the pillow. “This is… I can’t… I’m gonna…”

“You’re not,” Kenny stated, clenching around him internally, halting his motion. He held still, a statue astride him, until the crisis passed. Then he began again, a different pace, a different angle. Another hour bled away, measured in Stephen’s broken whimpers and the slick, rhythmic sound of their joining.

The third hour found Stephen a mindless, begging creature. Tears had wet the blindfold. His pleas were reduced to a single, shattered word. “Please. Please. Please.”

Kenny leaned forward, bracing his hands on Stephen’s heaving chest. He changed his motion to shallow, grinding circles that rubbed Stephen’s cock directly against his prostate. He lowered his head and took Stephen’s right nipple into his mouth again, laving it with his tongue. With his other hand, he finally wrapped a slick fist around the base of Stephen’s cock.

He stroked him in time with his own grinding hips. Fast. Purposeful.

“Now,” Kenny whispered against his chest, the word a hot benediction. “Come for me now. Give it all to me.”

It was the permission Stephen’s entire body had been screaming for. His orgasm tore through him like a seismic event. A raw, guttural shout was ripped from his throat as his cock pulsed violently in Kenny’s hand, jets of come streaking up between their bodies. He shook, his binds straining against the headboard, every muscle locking and releasing in a catastrophic wave.

Kenny rode him through it, milking him with his hand, until Stephen was completely spent, his cries fading into stunned, whimpering gasps. Only then did Kenny still, himself trembling with the force of the contained performance.

Kenny stayed seated on him, feeling the hot, wet mess between them, feeling the frantic pulse inside Stephen finally begin to slow. The air was a solid, soupy weight, thick with salt and sex. He reached up, his fingers finding the knot of the blindfold. He untied it, the black cloth falling away.

Stephen’s eyes blinked open, pupils blown wide, utterly unfocused. He stared at the ceiling as if he’d never seen it before.

“Are you done?” Kenny asked, his voice quiet but clear in the muffled room.

Stephen’s tongue, pale and dry, swiped over his lower lip. He didn’t look at Kenny. He just breathed, a ragged, wrecked sound. “I just need to… I need to lay down for awhile.”

A faint, knowing smile touched Kenny’s mouth. He’d heard that before from men who were spent but not finished, who were afraid the feeling would end. He leaned down, his lips brushing Stephen’s ear. “Then just relax.” He didn’t unlock the cuffs. He left Stephen’s arms tethered above his head, bound and open.

Kenny shifted, sliding off Stephen’s softening cock with a wet, loose sound. He settled beside him on the silk, propping himself up on an elbow. He looked at Stephen’s chest, at the nipples he’d worked into dark, swollen peaks. They were still hard, sensitive-looking in the dim light. He reached out and dragged the pad of his thumb, almost casually, over the left one.

Stephen jolted as if shocked, a broken gasp hiccupping from his throat. “Ah! Fuck, that’s… it’s too much.”

“It’s not too much,” Kenny murmured. He did it again, slower, applying more pressure. “You’re just feeling it. All of it.” He lowered his head and took the tight bud into his mouth, suckling with a gentle, persistent rhythm that was more maddening than any hard bite had been.

“No, no, wait, please,” Stephen begged, but his body arched into the touch, betraying him completely. His oversensitive nerves were alight, each pass of Kenny’s tongue a bolt of agonizing pleasure straight to his drained cock, which gave a pathetic, sympathetic twitch.

Kenny ignored him. He devoted himself to the task with a painter’s meticulous attention. He switched between the nipples, using his tongue, his lips, the very edges of his teeth. He’d lavish one for minutes until Stephen was shuddering and mewling, then move to the other, giving the first a moment of cruel, empty air before returning to it. He traced the areolas with the tip of his fingernail. He pinched and rolled, tugging until fresh tears leaked from the corners of Stephen’s eyes.

Time lost all shape. It was measured in Stephen’s hitched breaths, in the sheen of new sweat on his skin, in the gradual, reluctant reawakening of his body. Kenny’s own arousal, banked but never extinguished, began to coil tight again. He could feel the phantom ache from Alan, a deep, pleasant bruise that was now layered with the live-wire tension of holding Stephen here, on this knife-edge, for what felt like hours.

Stephen’s cock, impossibly, began to fill again. It was a slow, painful-looking resurrection, thickening against his stomach amidst the drying streaks of his first release. A thin, fresh pearl of pre-come welled at the tip.

Kenny saw it. He stopped his torture, sitting up. He reached for the lube again.

“Round two,” Kenny said, his voice no longer a murmur. It was a statement. He slicked his own hardness, the sound obscene. He positioned himself over Stephen, his knees bracketing those defined hips. He didn’t guide Stephen’s cock into him. He reached behind himself, took it in hand—it was fully hard now, leaking—and stroked it once, roughly. Then he aligned it and sank down.

The sensation was different this time. Deeper, hotter, filthier. Stephen was already used, already breached, and Kenny took him with a single, demanding plunge. He threw his head back, a sharp sigh escaping him. This was for him.

He set a punishing pace from the start, fucking himself on Stephen’s cock with a brutal, selfish rhythm. Each drop of his hips was a calculated slap of skin, a driven search for his own climax. He braced his hands on Stephen’s chest, fingernails digging in, using him as an anchor.

“You’re gonna… you’re gonna make me come again,” Stephen whispered, awed and horrified. His body was a live wire, strung too tight, sensation bombarding him from everywhere—the grip on his cock, the pain in his chest, the complete helplessness.

“I know,” Kenny grunted, his composure fracturing. “You’re gonna give it to me. And then you’re gonna fucking come for me. Again.” He rode him harder, his own need a crescendo in his veins. The memory of Alan’s phone chiming was a distant ghost. This was now. This was the raw, fucking truth of his body.

Kenny’s climax built like a storm surge. It was less an explosion than a total, sweeping collapse of control. His rhythm shattered into frantic, shallow jerks. A ragged, guttural cry tore from his throat, unlike any sound he’d made all night, raw and entirely his own. He came untouched, stripes of white painting Stephen’s stomach and chest, his body clamping down in vicious, pulsating waves around the cock inside him.

He shuddered through it, slumping forward for a moment, breathing in the scent of their collective ruin. Then, he forced his eyes open. He looked down at Stephen, whose face was a masterpiece of overwhelmed agony.

Kenny began to move again. Slow. Deliberate. He was impossibly tight, clenching rhythmically from his own orgasm. He reached down, wrapped his hand around the base of Stephen’s cock, and started to stroke him in time with his movements.

“Your turn,” Kenny panted, his voice hoarse. “I want to feel it. I want to feel you fucking lose it inside me. Now.”

The command, the friction, the overwhelming overstimulation broke Stephen completely. A sob ripped from him, his body bowing against the restraints. His release was a deep, internal pulse, a hot flood that felt endless. He cried out, a sound stripped of all language, as he emptied himself into Kenny for the second time, his vision whiting out at the edges.

Kenny milked him through it, until Stephen was limp, completely spent, his eyes rolling back before fluttering closed. Only then did Kenny climb off, his legs unsteady. He found the small keys in the leather case and unlocked the cuffs from the bedposts, then the manacles from Stephen’s wrists. He didn’t remove them entirely. He left the padded bracelets on, a final mark.

He collapsed beside Stephen on the ruined silk. Neither spoke. The heat of the room finally registered, a suffocating blanket. Sometime later, Stephen shifted, curling onto his side, his back to Kenny. Kenny stared at the ornate ceiling, feeling the slow cool trickle of Stephen’s release leaking from his body onto the sheets. He stayed until Stephen’s breathing evened out into true sleep, then he stood on trembling legs and walked to the shower.

The next morning, pale light filtered through the haze over the hills. Stephen was in the kitchen, wearing loose sweatpants, the cuff marks faint bruises on his wrists. He was sipping water, his movements slow. He looked younger, softer.

“There’s coffee,” he said, not looking at Kenny.

Kenny, dressed in last night’s clothes, poured a cup. They stood in silence, looking out at the city.

“That was…” Stephen began, then shook his head. “I don’t have the words.”

“You don’t need them,” Kenny said.

Stephen nodded. He picked up his phone from the counter, tapped it a few times. A moment later, Kenny’s own phone, in his pocket, vibrated once with a discreet, familiar chime. A notification. A transfer. Six hundred thousand dollars.

Stephen set his phone down. “Thank you,” he said, and the gratitude in his voice was real, heavy, and completely separate from the money.

Kenny finished his coffee, set the cup in the sink. He gave Stephen a last, easy smile—the chameleon’s smile, warm and professional. “Any time.”

He let himself out. The hallway carpet was silent under his shoes. The elevator descended smoothly. He walked through the gilded lobby, past the staring bellhops, and out into the sharp, smoggy brightness of the Beverly Hills morning. Another satisfied customer. Another payment. He got into his car, the leather seat hot. The phantom aches layered—Alan’s claiming, Stephen’s surrender—a complex map on his body. He started the engine and pulled into the traffic, another ghost in the city of light.

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